Anal intercourse poses a greater risk for human immunodeficiency virus (HIV) transmission than vaginal intercourse, and in recent years there has been a growing understanding that heterosexual anal intercourse (HAI) is not uncommon. However, the majority of the anal intercourse literature has focused on men who have sex with men. The little research on HAI has mostly looked at women, with limited work among men. This analysis examined the association between HAI and high-risk behaviors (N = 1,622) and sexual sensation seeking (N = 239) in a sample of men recruited from 2001 to 2012 in Long Beach, California. Almost half of the sample was non-Hispanic Black. The median age was 42 years, 42\% were homeless, and 20\% reported recent HAI. Men who reported HAI were likely to be Hispanic, were likely to be homeless, had a male partner, engaged in sex exchange, and used cocaine or amphetamines during sex. Men who reported HAI scored higher on the Sexual Sensation Seeking scale. This research supports other work showing the relationship between HAI and high-risk behaviors. More important, it contributes new knowledge by demonstrating the association between HAI and sexual sensation seeking. This research highlights the importance of personality traits when trying to understand sexual behavior and when developing HIV prevention interventions.